US4885033A - Pigment compositions based on acetoacetarylide derivatives - Google Patents

Pigment compositions based on acetoacetarylide derivatives Download PDF

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Publication number
US4885033A
US4885033A US07/248,078 US24807888A US4885033A US 4885033 A US4885033 A US 4885033A US 24807888 A US24807888 A US 24807888A US 4885033 A US4885033 A US 4885033A
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United States
Prior art keywords
acetoacet
pigment
component
pigment composition
composition according
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Expired - Lifetime
Application number
US07/248,078
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English (en)
Inventor
John B. Blackburn
Alexander Hamilton
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BASF Corp
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Ciba Geigy Corp
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Filing date
Publication date
Priority claimed from GB878723257A external-priority patent/GB8723257D0/en
Priority claimed from GB878724085A external-priority patent/GB8724085D0/en
Application filed by Ciba Geigy Corp filed Critical Ciba Geigy Corp
Assigned to CIBA-GEIGY CORPORATION reassignment CIBA-GEIGY CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CIBA-GEIGY AG, A SWISS CO.
Application granted granted Critical
Publication of US4885033A publication Critical patent/US4885033A/en
Assigned to CIBA SPECIALTY CHEMICAL CORPORATION reassignment CIBA SPECIALTY CHEMICAL CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CIBA-GEIGY CORPORATION
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0055—Mixtures of two or more disazo dyes

Definitions

  • the present invention relates to new pigment compositions, to their production and to their use in producing highly concentrated dispersions and inks for use in modern offset and letterpress inks.
  • a pigment composition comprising (a) a pigment derived from the mixed coupling of acetoacet-2-methylanilide and acetoacet-2,4-xylidide on to tetrazotised 3,3'-dichlorobenzidine, (b) a dyestuff derived from acetoacet-2,4-xylidide coupled on to tetrazotised benzidine-2,2'-disulfonic acid, and (c) disproportionated rosin, was considered but was found to be only just fluid at a pigment concentration of 35% by weight and, moreover, is colouristically weak.
  • a pigment composition containing (a) a pigment derived from the mixed coupling of acetoacet-2,4-xylidide and acetoacet-2-chloranilide on to tetrazotised 3,3'-dichlorobenzidine, (b) a dyestuff derived from tetrazotised benzidine-2,2'-disulfonic acid and acetoacet-2,4-xylidide and (c) the calcium salt of hydrogenated disproportionated rosin, while having adequate strength and good offset/letter press printing characteristics, could only provide adequate rheology when processed at pigment concentrations 35% by weight or less.
  • a pigment composition containing (a) a pigment obtained by coupling acetoacet-2,4-xylidide on to tetrazotised 3,3'-dichlorobenzidine (b) a dyestuff derived from tetrazotised benzidine-2,2'-disulfonic acid and acetoacet-2,4-xylidide and (c) disproportionated rosin gave the desired rheology at high pigment concentration, but the product was colouristically too weak to be of commercial interest.
  • publication gravure yellow pigments (which are e.g. Pigment Yellow 12 treated with amines) do not give satisfactory results in highly concentrated dispersions because of problems they create in terms of their water balance control on the press and their colouristic weakness.
  • the present invention provides a pigment compositon, suitable for use in modern offset and letter press inks, comprising:
  • the ratio of components (A) and (B) in the pigment composition of the invention ranging from 35:65 to 95:5.
  • the ratio ranges e.g. from 35:65 to 90:10% by weight, but preferably from 40:60 to 60:40% by weight.
  • the preferred pigment component A (a) is that derived by coupling a mixture of acetoacet-o-toluidide and acetoacet-2,4-xylidide on to tetrazotised 3,3'-dichlorobenzidine, so producing a mixture of dyes having the respective formulae I, II and III: ##STR1## Pigment I is, of course, Pigment Yellow 13 (C.I. 21100) and Pigment II is Pigment Yellow 14 (C.I. 21095).
  • the preferred dyestuff component A (b) is that derived form acetoacet-2,4-xylidide coupled on to tetrazotised benzidine-2,2'-disulfonic acid and having the formula IV: ##STR2##
  • component (A) of the pigment composition of the present invention optionally, but preferably contains a resin or resinous material.
  • Such resins or resinous materials are wood resin and its derivatives such as hydrogenated wood rosin and, in particular, disproportionated wood rosin, preferably at least in part present as its alkaline earth, especially its zinc salt.
  • the proportion, by weight, of the dyestuff component A (b) in the total pigment component (A) of the invention is minor, ranging e.g. from 0.5 to 10% by weight, more preferably from 0.75 to 5% by weight, based on total pigment component (A).
  • the major component is the pigment component A (a) which amounts generally to 50 to 75% by weight of total component (A).
  • component A (a) may contain from 15 to 45%, more preferably from 25 to 40% by weight of a resin component A (c), in particular a substantially 50:50 mixture by weight of (i) disproportionated wood rosin as free acid and (ii) disproportionated wood rosin as its salt.
  • the preferred pigment B (a) of the pigment composition of the invention is that derived by coupling acetoacetanilide on to tetrazotised 3,3'-dichlorobenzidine giving a pigment of formula V: ##STR3## Pigment of formula V is Pigment Yellow 12 (C.I. 21090).
  • the amines used as component B (b) of the pigment compositions of the invention are primary amines such as stearylamine; rosin amines e.g. amine derivatives of wood rosin ("®Rosin Amine D”); N-long chain alkylalkylenediamines (“®DUOMEENS”); polyamines e.g.
  • the preferred amine components B (b) are the N-alkyl-propylenediamine.
  • components (A) and (B) are prepared separately, including optional and preferred resination of component (A), and then to blend components (A) and (B) in the desired ratio.
  • the pigment compositions are particularly suitable for formulation into offset and letter press inks, in which they demonstrate excellent high pigment loadability (up to 55% by weight of pigment), while exhibiting good rheology under ink processing conditions, as well as good printing and colouristic properties.
  • the ink will normally be formulated by firstly preparing, e.g. in a bead mill, a concentrate based on a solvent base, a hyperdispersant and a resin and a high loading (35-50% by weight) of pigment.
  • Typical ingredients of the concentrate are:
  • Solvent base which constitutes at least 50% by weight of the ink and customarily comprises mainly aliphatic hydrocarbon distillate fraction of boiling points within the range 240° C. to 310° C.;
  • Hyperdispersant constituting 0 to 10% by weight of the ink, for example, the dispersing agents derived from e.g. poly(12-hydroxystearic acid) and dimethylaminopropylamine in an organic liquid e.g. toluene as described in U.S. Pat. No. 4,461,647;
  • Resins constituting 0-20% by weight of the ink composition and comprising for example an alkyd resin, a rosin-modified phenolic resin or a rosin ester;
  • aqueous tetrazo solution prepared from 220 g of 3,3'-dichlorobenzidine is coupled to a mixed slurry containing 250 g of acetoacet-2,4-xylidide and 100 g of acetoacet-2-toluidide buffered at pH 4.0-5.0.
  • the resulting pigment slurry is neutralised and a solution containing 12.5 g of water-soluble azo dyestuff prepared from tetrazotised benzidine-2,2'-disulphonic acid and acetoacet-2,4-xylidide is added followed by an aqueous solution of 260 g of a disproportionated wood rosin as its sodium salt.
  • the mixture is heated to 95° C.
  • aqueous tetrazo solution prepared from 300 g of 3,3'-dichlorobenzidine is coupled to 450 g of acetoacetanilide, then the product is slurried in an aqueous solution containing 140 g of a mixed alkylaminopropylamine as its acetate salt (®DINORAM 42), in which the number of carbon atoms in the alkyl groups falls predominantly in the range C 18 -C 22 , while maintaining the pH at 4.5.
  • the pH is adjusted to 11.7 and the mixture is heated to 95° C. and held at 95° C. for 60 minutes.
  • the pigment is isolated by filtration, washed free of impurities with water, and dried at 80° C. to give the final product.
  • a dispersion vehicle is prepared having the following composition:
  • An ink is prepared from the pigmented vehicle by adding offset ink varnishes (solution, in aliphatic hydrocarbon distillate, of rosin-modified phenolic resin and alkyd resin).
  • aqueous tetrazo solution prepared from 175 g of 3,3'-dichlorobenzidine is coupled to a slurry containing 285 g of acetoacet-2,4-xylidide and 29.4 g of a product prepared as described in example 1B, while maintaining the pH at 4.5-5.0.
  • 75 g of acetoacet-2-chloranilide are then added followed by a tetrazo solution prepared from 44 g of 3,3'-dichlorobenzidine.
  • the pigment slurry formed is neutralised and a solution containing 11.9 g of the azo dyestuff from benzidine-2,2'-disulphonic acid coupled to acetoacet-2,4-dimethylanilide is added followed by an aqueous alkaline solution of 200 g of ®STAYBELITE Resin as its sodium salt.
  • the mixture is heated to 95° C. and an aqueous solution containing 19.6 g of calcium chloride is added, followed by dilute hydrochloric acid to give a pH of 5.5.
  • the mixture is held at 90°-95° C. for further 60 minutes and the product is then isolated by filtration, washing free of water-soluble impurities with water and drying at 80° C.
  • Product A is made using the process described in example 1A but retaining the product in aqueous slurry form.
  • Product B is made using the process described in example 1B but using 488 g of the alkylaminopropylamine in place of 140 g and retaining the product in aqueous filtercake form.
  • Slurry containing 88.2 g of Product A is mixed with slurry containing 11.8 g of product B.
  • the final product is obtained by filtration, washing free of water-soluble impurities, and drying at 70° C.
  • Product A corresponds exactly to Product A in example 5.
  • Product C is made using the process described in example 1B but using 868 g of the alkylaminopropylamine in place of 140 g and retaining the product in aqueous filtercake form.
  • ®TRINORAM S N-alkyl dipropylene triamine, in which the number of carbon atoms in the alkyl group falls predominantly in the range C 16 -C 18 ).
  • ®POLYRAM S N-alkylpolypropylene polyamine, in which the number of carbon atoms in the alkyl chain falls predominantly in the range C 16 -C 18

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coloring (AREA)
US07/248,078 1987-10-03 1988-09-23 Pigment compositions based on acetoacetarylide derivatives Expired - Lifetime US4885033A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB878723257A GB8723257D0 (en) 1987-10-03 1987-10-03 Pigment compositions
GB8723257 1987-10-03
GB8724085 1987-10-14
GB878724085A GB8724085D0 (en) 1987-10-14 1987-10-14 Pigment compositions

Publications (1)

Publication Number Publication Date
US4885033A true US4885033A (en) 1989-12-05

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Family Applications (1)

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US07/248,078 Expired - Lifetime US4885033A (en) 1987-10-03 1988-09-23 Pigment compositions based on acetoacetarylide derivatives

Country Status (9)

Country Link
US (1) US4885033A (de)
EP (1) EP0311560B1 (de)
JP (1) JP2697873B2 (de)
KR (1) KR960007937B1 (de)
CA (1) CA1330850C (de)
DE (1) DE3854615D1 (de)
DK (1) DK171488B1 (de)
ES (1) ES2078898T3 (de)
MX (1) MX171414B (de)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000354A1 (en) * 1990-06-27 1992-01-09 Ferro Corporation Liquid colorant/additive concentrate for incorporation into plastics
US5246494A (en) * 1991-07-23 1993-09-21 Engelhard Corporation Mixed coupled azo pigments
US5306342A (en) * 1991-06-06 1994-04-26 Ciba-Geigy Corporation Production of pigments
US6099635A (en) * 1999-04-09 2000-08-08 Lonza Ag Acetoacetylated suspensions in pigment applications
US6488759B1 (en) 2001-08-27 2002-12-03 Engelhard Corporation Strong monoarylide pigment/hydrocarbyl polypropyleneamine compositions
US20030096054A1 (en) * 2000-01-14 2003-05-22 Rick Green Dried honey enriched with volatile honey compounds
WO2005037929A1 (de) * 2003-10-16 2005-04-28 Clariant Produkte (Deutschland) Gmbh Azopigmentpräparationen für den verpackungstief- und flexodruck
US20080312358A1 (en) * 2005-11-28 2008-12-18 Agfa Graphics Nv Non-Aqueous Pigment Dispersions Containing Specific Dispersion Synergists
CN101942209A (zh) * 2010-08-21 2011-01-12 维波斯新材料(潍坊)有限公司 用4-乙酰乙酰氨基苯膦酸盐改性的偶氮黄色颜料的制备方法
US20110061564A1 (en) * 2008-04-18 2011-03-17 Russell Schwartz Diarylide Yellow Pigments
CN104263002A (zh) * 2014-08-19 2015-01-07 上虞市东海化工有限公司 一种黄色颜料的制备方法
CN106590016A (zh) * 2016-12-06 2017-04-26 杭州荣彩实业有限公司 一种混晶型c.i.颜料黄12的生产方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2235694B (en) * 1989-08-10 1992-06-24 Ciba Geigy Ag Process for the preparation of bisazo pigment mixtures
DE19806397B4 (de) * 1997-04-11 2006-07-06 Basf Ag Pigmentzubereitungen in Granulatform auf Basis von mit Harzsäure/Harzseife-Gemischen belegten organischen Pigmenten
JP3885503B2 (ja) 2000-04-10 2007-02-21 東洋インキ製造株式会社 ジスアゾ顔料の製造方法
JP5232973B2 (ja) * 2011-11-02 2013-07-10 東洋インキＳｃホールディングス株式会社 ジスアゾ顔料組成物およびその製造方法、印刷インキ組成物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3776749A (en) * 1970-05-06 1973-12-04 Ciba Geigy Ag Diarylide pigment compositions
US4461647A (en) * 1981-08-11 1984-07-24 Imperial Chemical Industries Limited Fluidizing agent
US4474609A (en) * 1978-12-20 1984-10-02 Hoechst Aktiengesellschaft Recrystallization-resistant monoazo pigment mixtures of high tinctorial strength, process for their preparation and their use
US4720304A (en) * 1984-09-19 1988-01-19 Basf Farben+Fasern Aktiengesellschaft Pigment formulations
US4810302A (en) * 1984-05-11 1989-03-07 Toyo Ink Manufacturing Co., Ltd. Azo pigment composition

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2012152C3 (de) * 1970-03-14 1974-03-21 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Verfahren zur Herstellung von Pigmentfarbstoffgemischen aus Disazofarbstoffen und deren Verwendung
GB1356253A (en) * 1970-05-06 1974-06-12 Ciba Geigy Uk Ltd Azo pigment compositions
FR2376192A1 (fr) * 1976-12-30 1978-07-28 Ugine Kuhlmann Nouvelles compositions pigmentaires jaunes destinees aux encres d'imprimerie
US4341701A (en) * 1979-11-07 1982-07-27 Ciba-Geigy Corporation Production of pigments
US4680057A (en) * 1985-04-12 1987-07-14 Basf Corporation, Inmont Division Easily flushable transparent, strong diarylide yellow pigment compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3776749A (en) * 1970-05-06 1973-12-04 Ciba Geigy Ag Diarylide pigment compositions
US4474609A (en) * 1978-12-20 1984-10-02 Hoechst Aktiengesellschaft Recrystallization-resistant monoazo pigment mixtures of high tinctorial strength, process for their preparation and their use
US4461647A (en) * 1981-08-11 1984-07-24 Imperial Chemical Industries Limited Fluidizing agent
US4810302A (en) * 1984-05-11 1989-03-07 Toyo Ink Manufacturing Co., Ltd. Azo pigment composition
US4720304A (en) * 1984-09-19 1988-01-19 Basf Farben+Fasern Aktiengesellschaft Pigment formulations

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
E. W. Flinck, "Printing Ink Formulations", Noyes, pp. 110 and 177.
E. W. Flinck, Printing Ink Formulations , Noyes, pp. 110 and 177. *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000354A1 (en) * 1990-06-27 1992-01-09 Ferro Corporation Liquid colorant/additive concentrate for incorporation into plastics
US5157067A (en) * 1990-06-27 1992-10-20 Ferro Corporation Liquid colorant/additive concentrate for incorporation into plastics
US5308395A (en) * 1990-06-27 1994-05-03 Ferro Corporation Liquid colorant/additive concentrate for incorporation into plastics
US5306342A (en) * 1991-06-06 1994-04-26 Ciba-Geigy Corporation Production of pigments
US5246494A (en) * 1991-07-23 1993-09-21 Engelhard Corporation Mixed coupled azo pigments
USRE35654E (en) * 1991-07-23 1997-11-11 Engelhard Corporation Mixed coupled azo pigments
US6099635A (en) * 1999-04-09 2000-08-08 Lonza Ag Acetoacetylated suspensions in pigment applications
US7101582B2 (en) * 2000-01-14 2006-09-05 Huny Hunks Ltd. Dried honey enriched with volatile honey compounds
US20030096054A1 (en) * 2000-01-14 2003-05-22 Rick Green Dried honey enriched with volatile honey compounds
US6488759B1 (en) 2001-08-27 2002-12-03 Engelhard Corporation Strong monoarylide pigment/hydrocarbyl polypropyleneamine compositions
WO2005037929A1 (de) * 2003-10-16 2005-04-28 Clariant Produkte (Deutschland) Gmbh Azopigmentpräparationen für den verpackungstief- und flexodruck
US20070204762A1 (en) * 2003-10-16 2007-09-06 Heinz Bach Azo Pigment Preparations for Packaging Gravure and Flexographic Printing
US7318863B2 (en) 2003-10-16 2008-01-15 Clariant Produkte (Deutschland) Gmbh Azo pigment preparations for packaging gravure and flexographic printing
US8022117B2 (en) * 2005-11-28 2011-09-20 Agfa Graphics Nv Non-aqueous pigment dispersions containing specific dispersion synergists
US20080312358A1 (en) * 2005-11-28 2008-12-18 Agfa Graphics Nv Non-Aqueous Pigment Dispersions Containing Specific Dispersion Synergists
US8034174B2 (en) * 2008-04-18 2011-10-11 Sun Chemical Corporation Diarylide yellow pigments
US20110061564A1 (en) * 2008-04-18 2011-03-17 Russell Schwartz Diarylide Yellow Pigments
CN101942209A (zh) * 2010-08-21 2011-01-12 维波斯新材料(潍坊)有限公司 用4-乙酰乙酰氨基苯膦酸盐改性的偶氮黄色颜料的制备方法
CN101942209B (zh) * 2010-08-21 2013-03-20 维波斯新材料(潍坊)有限公司 用4-乙酰乙酰氨基苯膦酸盐改性的偶氮黄色颜料的制备方法
CN104263002A (zh) * 2014-08-19 2015-01-07 上虞市东海化工有限公司 一种黄色颜料的制备方法
CN106590016A (zh) * 2016-12-06 2017-04-26 杭州荣彩实业有限公司 一种混晶型c.i.颜料黄12的生产方法

Also Published As

Publication number Publication date
CA1330850C (en) 1994-07-26
ES2078898T3 (es) 1996-01-01
JP2697873B2 (ja) 1998-01-14
EP0311560A2 (de) 1989-04-12
DK546288A (da) 1989-04-04
DE3854615D1 (de) 1995-11-30
EP0311560A3 (de) 1991-06-05
DK171488B1 (da) 1996-11-25
KR890006759A (ko) 1989-06-15
JPH01110578A (ja) 1989-04-27
MX171414B (es) 1993-10-26
KR960007937B1 (ko) 1996-06-17
DK546288D0 (da) 1988-09-30
EP0311560B1 (de) 1995-10-25

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